Sodium Carbonate → 6-Fluoro-5-(5-hydroxymethyl-pyridin-3-yl)-3-methyl-3H-benzooxazol-2-one

Participants

Reaction Conditions

Reaction Steps

A mixture of 6-Fluoro-3-methyl-5-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-3H-benzooxazol-2-one (352 mg, 1.2 mmol), (5-bromopyridin-3-yl)methanol (188 mg, 1 mmol), Na2CO3 (2 M in water, 1 mL, 2 mmol), polymer bound Pd(PPh3)4 (642 mg, 0.07 mmol) in DME (4 mL) was heated by microwave at 100° C. for 1.25 h. The reaction mixture was cooled to room temperature and the mixture was diluted with CH3OH/CH2Cl2 (1:1, 50 mL) and filtered through a pad of celite. The celite pad was further washed with CH2Cl2/CH3OH (50 mL). Ater concentration, the residue was purified by flash column (0-10%, v/v, CH3OH in CH2Cl2) and afforded 121.9 mg of the desired product as a white solid. ESI-MS m/z: 274.9 [M+1]+, Retention time 0.93 min; 1HNMR (MeOD, 400.342 MHz) δ 3.44 (s, 3H), 4.74 (s, 2H), 7.30 (d, J=9.7 Hz, 1H), 7.34 (d, J=6.4 Hz, 1H), 8.03 (s, 1H), 8.55 (s, 1H), 8.64 (s, 1H)

Provenance & Evidence